TY - JOUR
T1 - Examination of chlorin-bacteriochlorin energy-transfer dyads as prototypes for near-infrared molecular imaging probes
AU - Kee, Hooi Ling
AU - Nothdurft, Ralph
AU - Muthiah, Chinnasamy
AU - Diers, James R.
AU - Fan, Dazhong
AU - Ptaszek, Marcin
AU - Bocian, David F.
AU - Lindsey, Jonathan S.
AU - Culver, Joseph P.
AU - Holten, Dewey
PY - 2008/9
Y1 - 2008/9
N2 - New classes of synthetic chlorin and bacteriochlorin macrocycles are characterized by narrow spectral widths, tunable absorption and fluorescence features across the red and near-infrared (NIR) regions, tunable excited-state lifetimes (<1 to >10 ns) and chemical stability. Such properties make dyad constructs based on synthetic chlorin and bacteriochlorin units intriguing candidates for the development of NIR molecular imaging probes. In this study, two such dyads (FbC-FbB and ZnC-FbB) were investigated. The dyads contain either a free base (Fb) or zinc (Zn) chlorin (C) as the energy donor and a free base bacteriochlorin (B) as the energy acceptor. In both constructs, energy transfer from the chlorin to bacteriochlorin occurs with a rate constant of ∼(5 ps)-1 and a yield of >99%. Thus, each dyad effectively behaves as a single chromophore with an exceptionally large Stokes shift (85 nm for FbC-FbB and 110 nm for ZnC-FbB) between the red-region absorption of the chlorin and the NIR fluorescence of the bacteriochlorin (λf = 760 nm, Φf = 0.19, τ ∼ 5.5 ns in toluene). The long-wavelength transitions (absorption, emission) of each constituent of each dyad exhibit narrow (≤20 nm) spectral widths. The narrow spectral widths enabled excellent selectivity in excitation and detection of one chlorin-bacteriochlorin energy-transfer dyad in the presence of the other upon diffuse optical tomography of solution-phase phantoms.
AB - New classes of synthetic chlorin and bacteriochlorin macrocycles are characterized by narrow spectral widths, tunable absorption and fluorescence features across the red and near-infrared (NIR) regions, tunable excited-state lifetimes (<1 to >10 ns) and chemical stability. Such properties make dyad constructs based on synthetic chlorin and bacteriochlorin units intriguing candidates for the development of NIR molecular imaging probes. In this study, two such dyads (FbC-FbB and ZnC-FbB) were investigated. The dyads contain either a free base (Fb) or zinc (Zn) chlorin (C) as the energy donor and a free base bacteriochlorin (B) as the energy acceptor. In both constructs, energy transfer from the chlorin to bacteriochlorin occurs with a rate constant of ∼(5 ps)-1 and a yield of >99%. Thus, each dyad effectively behaves as a single chromophore with an exceptionally large Stokes shift (85 nm for FbC-FbB and 110 nm for ZnC-FbB) between the red-region absorption of the chlorin and the NIR fluorescence of the bacteriochlorin (λf = 760 nm, Φf = 0.19, τ ∼ 5.5 ns in toluene). The long-wavelength transitions (absorption, emission) of each constituent of each dyad exhibit narrow (≤20 nm) spectral widths. The narrow spectral widths enabled excellent selectivity in excitation and detection of one chlorin-bacteriochlorin energy-transfer dyad in the presence of the other upon diffuse optical tomography of solution-phase phantoms.
UR - http://www.scopus.com/inward/record.url?scp=50849142560&partnerID=8YFLogxK
U2 - 10.1111/j.1751-1097.2008.00409.x
DO - 10.1111/j.1751-1097.2008.00409.x
M3 - Article
C2 - 18673324
AN - SCOPUS:50849142560
SN - 0031-8655
VL - 84
SP - 1061
EP - 1072
JO - Photochemistry and Photobiology
JF - Photochemistry and Photobiology
IS - 5
ER -